Hydrochloric Acid → 2-(3-Hydroxyphenoxymethyl)-6-methylbenzoic Acid

HRID 731129노트

반응식

HRID 731129 반응식
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:9](=[O:10])[O:8][CH2:7]2.[C:12]1([CH:19]=[CH:18][CH:17]=[C:15]([OH:16])[CH:14]=1)[OH:13].CC(C)([O-])C.[K+].Cl>CN1CCCC1=O.O>[OH:13][C:12]1[CH:14]=[C:15]([CH:17]=[CH:18][CH:19]=1)[O:16][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]([CH3:7])[C:11]=1[C:9]([OH:10])=[O:8]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 5054ResorcinolHCID 6387577-methyl-2-benzofuran-1(3H)-oneHCID 23665647Potassium tert-butoxide2회

생성물 1

HCID 114253992-(3-Hydroxyphenoxymethyl)-6-methylbenzoic Acid수율 77.7%

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
140 °C

실험 절차

7-Methylphthalide (30.1 g, 203 mmol), resorcinol (45.3 g, 407 mmol) and potassium tert-butoxide (47.6 g, 424 mmol) are suspended in 300 ml of N-methylpyrrolidone (NMP) and stirred at 140° C. for 21 h. After this time, a second amount of potassium tert-butoxide (2.4 g, 21.4 mmol) is added and stirring is continued at 140° C. for 2.5 h. The reaction mixture is cooled, 800 ml of water are added, and the mixture is acidified to pH=2 at 20° C. with concentrated hydrochloric acid. After stirring at 3 to 5° C. for 2 hours, the pale beige solid is filtered off with suction, washed with water and then dried. The isolated product contains 2-(3-hydroxyphenoxymethyl)-6-methylbenzoic acid and N-methylpyrrolidone as solvate molecule in a ratio of 1:1. Yield 77.7%, melting point 98 to 99° C.

후처리

  1. stirringstirring
  2. waitis continued at 140° C. for 2.5 h
  3. temperatureThe reaction mixture is cooled
  4. stirringAfter stirring at 3 to 5° C. for 2 hours
  5. filtrationthe pale beige solid is filtered off with suction
  6. washwashed with water
  7. customdried

출처 및 근거

ORD 기록
ord-b6f4f973b1b44949ae093f4986a5979a
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582794B2

반응 노트

불러오는 중…